Holiday rentals with a pool in Manatee County

A single-story home is framed by a green lawn and shaded by large trees. The exterior features a light blue color with a red roof. A driveway leads to a one-car garage, and a wooden fence provides privacy in the background.

4.99 out of 5 average rating, 83 reviews

Cozy & spacious home with heated pool

Live the Florida lifestyle in our cozy home! Wake up and enjoy coffee by the pool with a serene lake view. Nearby you will find nature preserves amazing beaches Siesta Key and Coquina Beach on Anna Maria Island kayaking activities fishing etc Spend the evening walking along Riverwalk and grabbing dinner on the water. We are close to Sarasota or St. Pete. Found right in the middle of everything Florida has to offer this home is perfect for those looking to explore and relax in a peaceful setting

Superhost

5 out of 5 average rating, 4 reviews

The Modern Farmstead w/ Pool Spa & Games

The Modern Farmstead is a home designed for families and group getaways, located on a shared property fully dedicated to Airbnb stays. ‼️An attached guest house on the property is also an Airbnb‼️ Each unit has its own private entrance, with no shared interior spaces or interior access between units, allowing guests to enjoy privacy while staying on the same property. Parking is shared between both units. This Airbnb has three reserved parking spots look for the parking signs on the fence .

A modern bedroom features a four-poster bed dressed in neutral linens, complemented by wall-mounted lamps. A decorative bench is placed at the foot of the bed. Natural light fills the room through large sliding glass doors that open to a private balcony.

4.92 out of 5 average rating, 144 reviews

4BR Golf View-Heated Pool/IMG Academy/Near Beaches

Welcome to The Cortez Retreat! We are delighted to have you. This gorgeous home has been completely renovated in a peaceful neighborhood overlooking the IMG Golf Course. Pack your bags and get ready to escape to SW Bradenton, just 6 miles from SRQ Airport and 10 miles from downtown Sarasota. Siesta Key has been rated the #1 beach in the US, only 17 miles from the home. Additionally, Ana Maria Island is 11 miles, Lido Beach 12 miles, Coquina Beach 9 miles, and Longboat Key 12 miles from home!

4.98 out of 5 average rating, 127 reviews

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

Home in Sarasota

Sunshine House, near Downtown, Legacy Trail, Beach

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

4.93 out of 5 average rating, 123 reviews

An outdoor area features a heated pool surrounded by a spacious deck. Lounge chairs are positioned nearby for relaxation, and a dining set offers seating for outdoor meals. A screened enclosure provides protection from insects while allowing natural light to filter through.

Home in Sarasota

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

A private pool area is enclosed by a screened lanai, featuring a white water slide extending from one side. Sun loungers are positioned nearby on the patio, with lush greenery visible in the background. The pool is surrounded by a spacious deck, inviting swimming and relaxation.

4.94 out of 5 average rating, 18 reviews

Sport & Wellness Getaways

Perfect for large families or group getaways, this luxury retreat features a private pool, game room, and expansive outdoor spaces. Highlights: * On-site property manager * Private pool and outdoor shower * BBQ area and large patio * Game room for all ages * Fully stocked kitchen * Unlimited outdoor parking + 2 covered spaces * Access to: 6 tennis courts (5 hard, 1 clay), 4 pickleball courts, 1 sand volleyball court * Shared Courtyard restrooms

4.86 out of 5 average rating, 138 reviews

Home in Longboat Key

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Apartment in Longboat Key

4.98 out of 5 average rating, 229 reviews

Sun-Kissed Memories!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

A screened-in private pool area is visible, featuring clear water that reflects sunlight. The surrounding yard is spacious and fenced, providing a serene environment for relaxation.

4.95 out of 5 average rating, 22 reviews

Pool house(pets ok) Sarasota beaches, UTC mall.

Welcome to Coastal Manor, a refined coastal retreat in Bradenton, FL. This elegant 3BR, 2.5BA home offers a serene escape with a private heated pool, spacious fenced yard, and pet-friendly amenities. Located in Lakewood Ranch just minutes from UTC, Nathan Benderson Park, Premier Sports, IMG Academy and Gulf Coast beaches. It’s the perfect blend of charm and convenience. Designed with a muted coastal cottage vibe, this getaway invites you to relax, unwind, and explore the best of Florida.

5 out of 5 average rating, 19 reviews

Garden Home/Heated Pool/King-Bed/20 min Beach/Pets

Nestled beneath towering trees, this cozy 3-bedroom, 2-bathroom home offers a peaceful getaway. The screened-in heated pool and patio provide a quiet spot to relax and enjoy nature’s beauty in privacy. With new beds and many thoughtful amenities, it’s a comfortable retreat for your stay. Whether you're swimming, grilling, or simply enjoying the surroundings, this home offers a calm atmosphere to unwind and share time with family or friends in complete comfort. Message us with questions.

An inviting exterior view of Sunrise Villa showcases a well-maintained landscape featuring lush greenery and vibrant plants. A spacious driveway leads up to a garage, with decorative stone detailing accentuating the garden area. The home is framed by palm trees, contributing to the tropical ambiance.

5 out of 5 average rating, 112 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

Relax with the family at this tropical oasis. Sunrise Villa sits in the corner of a quiet cul-de-sac, just a quarter mile from Palma Sola Bay and 5 miles from the quaint island of Anna Maria and its sandy white beaches. Enjoy the tropical backyard paradise and the abundance of restaurants, beaches, and entertainment in close proximity. Lounge by the pool, take a bike ride along the bay, take a short bike/car ride over to the island, or take a short car ride to downtown Bradenton.

A spacious patio is highlighted by a heated pool, surrounded by a decorative stone border. Comfortable outdoor seating is arranged nearby, beneath string lights that create a soft glow. A serene water view and lush greenery are visible in the background, enhancing the outdoor ambiance.